Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions
An enantioselective 1,4-conjugate addition of nitromethane to β-silyl α,β-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of β-silyl nitroalkanes in good to excellent yields (up to 92%) and enantioselectivitie...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2021-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.17.177 |
| _version_ | 1819004183867555840 |
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| author | Akhil K. Dubey Raghunath Chowdhury |
| author_facet | Akhil K. Dubey Raghunath Chowdhury |
| author_sort | Akhil K. Dubey |
| collection | DOAJ |
| description | An enantioselective 1,4-conjugate addition of nitromethane to β-silyl α,β-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of β-silyl nitroalkanes in good to excellent yields (up to 92%) and enantioselectivities (up to 97.5% ee) under solvent-free conditions at room temperature. Control experiments reveal that the presence of a β-silyl group in the enones is crucial for high reactivity under the optimized reaction conditions. |
| first_indexed | 2024-12-20T23:32:51Z |
| format | Article |
| id | doaj.art-4df93488ee564fb4975d8c6664bc3734 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T23:32:51Z |
| publishDate | 2021-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-4df93488ee564fb4975d8c6664bc37342022-12-21T19:23:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-10-011712642264910.3762/bjoc.17.1771860-5397-17-177Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditionsAkhil K. Dubey0Raghunath Chowdhury1Bio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, IndiaBio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, IndiaAn enantioselective 1,4-conjugate addition of nitromethane to β-silyl α,β-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of β-silyl nitroalkanes in good to excellent yields (up to 92%) and enantioselectivities (up to 97.5% ee) under solvent-free conditions at room temperature. Control experiments reveal that the presence of a β-silyl group in the enones is crucial for high reactivity under the optimized reaction conditions.https://doi.org/10.3762/bjoc.17.177β-silyl α,β-unsaturated carbonyl compoundsβ-silyl nitroalkaneschiral organosilanesorganocatalysissolvent-free synthesis |
| spellingShingle | Akhil K. Dubey Raghunath Chowdhury Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions Beilstein Journal of Organic Chemistry β-silyl α,β-unsaturated carbonyl compounds β-silyl nitroalkanes chiral organosilanes organocatalysis solvent-free synthesis |
| title | Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions |
| title_full | Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions |
| title_fullStr | Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions |
| title_full_unstemmed | Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions |
| title_short | Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions |
| title_sort | solvent free synthesis of enantioenriched β silyl nitroalkanes under organocatalytic conditions |
| topic | β-silyl α,β-unsaturated carbonyl compounds β-silyl nitroalkanes chiral organosilanes organocatalysis solvent-free synthesis |
| url | https://doi.org/10.3762/bjoc.17.177 |
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